After being dumped out of UEFA Champions League qualifying, Hearts now begin their bid to make the Europa League main phase when they take on Benfica over two legs.
The Scottish Premiership side were humbled by Sturm Graz in the second qualifying round of Europe's biggest competition, losing 4-0 away and 2-0 at home, so they have now slipped down to the Europa League.
Thursday's first leg against Benfica in Lisbon comes at the third qualifying round stage after the Portuguese giants beat St Gallen 6-2 on aggregate in the previous round.
Best Bet - Benfica to win to nil @ 5/6
Alternative Bet - Benfica to win 3-0 @ 13/2
Bet Builder - Over 2.5 total Benfica goals, HT/FT - Benfica/Benfica and Over 10 corners @ 11/4
Best Bet - Benfica to win to nil @ 5/6
After Hearts lost both legs of their contest with Sturm Graz to nil, they look set to be in for a familiar tale of woe up against Benfica at Estadio da Luz.
It has been a difficult summer for the Jambos following their gut-wrenching defeat on the final day of last season at Celtic that finally ended their Scottish Premiership title dream.
Manager Derek McInnes and top-scorer Lawrence Shankland have both departed for Rangers, they were embarrassed in their first appearance back in the UEFA Champions League in 20 years and then suffered late agony in their league opener at Aberdeen on Saturday.
The 2-1 result at Pittodrie was particularly frustrating as Hearts had led from the 35th minute with the Dons' equaliser not coming until the 90th minute, while the winner, from the penalty spot, was then blasted home by Kevin Nisbet deep into stoppage time.
However, they must quickly forget about that as they switch focus back to Europe.
New boss Wouter Vrancken could hardly have asked for a more difficult assignment when dropping into the continent's second competition as they go up against a Benfica side who are 1/20 to qualify, while Vrancken's men are a huge 10/1 to make it past this round.
Hearts will do all they can to ensure they are still in the tie for the return game at Tynecastle next week but the Eagles ominously hammered St Gallen 5-0 at home after losing the first leg 2-1 and they should dominate again.
Alternative Bet - Benfica to win 3-0 @ 17/2
With Benfica tipped to enjoy the bulk of possession and create more chances at home, a punt on a 3-0 first-leg scoreline might be worth taking.
Vrancken insisted the 4-0 defeat in Austria was harsh on his side given the chances they created, and he will now have to come up with a plan to prevent a repeat in Lisbon.
However, Benfica, who have former Fulham boss Marco Silva in charge, have plenty of attacking threat, not least Vangelis Pavlidis, who banged in four of the five goals against St Gallen.
Over 2.5 total Benfica goals
HT/FT - Benfica/Benfica
Over 10 corners
Pays 11/4
Backing Benfica to score at least three times forms the first leg of the Bet Builder, something the Eagles have managed in three of their last five competitive home matches, while Silva's side look likely to be in front at half-time before then going on to see out the first leg to a successful conclusion.
Hearts were 1-0 behind at the break in Graz, while Benfica held an identical advantage at half-time in their home tie with St Gallen.
There seems a strong chance of over 10 corners in Lisbon, too, with Benfica winning nine against the Swiss outfit in a second leg which had 11 corners in total, while there were 16 corners in Hearts' first-leg defeat against Sturm Graz, 12 of which were awarded to them.
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Benfica beat St Gallen in the second qualifying round, winning 5-0 at home after losing 2-1 away
Hearts were knocked out of the UEFA Champions League qualifiers 6-0 on aggregate by Sturm Graz
Benfica have been European champions twice, in 1961 and 1962
The Eagles have never won the UEFA Cup/Europa League but have been beaten finalists three times - in 1983, 2013 and 2014
Since the UEFA Cup was renamed the Europa League in 2009, Hearts have reached the play-off round five times but never progressed further
Whoever loses over the two legs will drop down into the Conference League play-off round
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This article was written by a partner sports writer via Spotlight Sports Group. All odds displayed on this page were correct at the time of writing and are subject to withdrawal or change at any time.